Octadionols.



UNITED STATES PATENT OFFICE.

GEORG MERLING AND HUGO KUHLER, F ELBERFELD, GERMANY, ASSIGNORS T0 FABBENFABRIKEN VORM. FRIEDR. BAYER & (30., 0F ELBERFELD, GERMANY, A

CORP ORATION OF GERMANY.

OCTADIONOLS.

No Drawing.

To all whom it may concern:

Be it known. that we, Gnono MnnmNo, professor of chemistry, doctor 01. philosopl'iy, and I-Inoo Konma, doctor of philosophy, citizens of the German Empire. residing at Elberteld, Germany, have invented new and useful Improvements in Octadionols, of which the following is a specification.

The present invention relates to the manufacture and production of the hitherto un known octadionols. The process for their production consists in treating methylene lretones with alkaline condensing agents of a mild action, such as carbonates of alkalis,

' borax, sodium phosphate, in heating methylene ketones or their homologues with water with or without the addition of acids, such as formic acid or by the addition of water to octeneclione or its homologues. On starting a. g. from methyleneethylmethyllretone the saturated 1.5-diketone (dimethyloctadionol) The new bodies are valuable intermediate compounds for producing pharmaceutical products or other technically valuable products. They are limpid oils soluble in water, ether, alcohol and benzene.

In order to illustrate the new process more fully the following examples are given, the parts being by weight Example 1: In a vessel provided with a reflux condenser a solution of 200 parts of methylene-ethylmethylketone in 6000 parts of water and from 5 to parts of concentrated formic acid is heated on the water bath during from to hours. Unchanged methylene-methylethylketone is removed by distillation with steam and 20 arts of anhydrous sodium carbonate are added to the liquid in the vessel. After cooling the solution is saturated with common salt, filtered and the filtrate is extracted with ether. The ethereal solution is dried Specification of Letters Patent.

Application filed June 2-8, 1910.

Patented May 9, 1911 Serial No. 569,330.

over potassium carbonate and the other is distilled oil. D1methyloctadionol. remains. Its vformation takes probably place according to the Following formula:

2crn=owns co---om+mo= on cn )-oo--o1n CT-I2-COGIi(CI-I3)CH1.OH.

It is a limpid oil soluble in water. boiling at 148 C. under a pressure of 18 mm. Its seniicarbazone melts at 209-210 C.

Example 2: 100 parts of methylene acetone are allowed to stand during 23 days with a solution of 510 parts of K CO in 1500 parts of water until the intense smell of methylene acetone has disappeared. The solution is then acidulated with tartaric acid, saturated with ammonium sulfate and is extracted several times with ether. The ethereal solutions are dried over sodium sulfate, and the ether is distilled over. A limpid oil remains boiling at 80-170 C. under a pressure of 21 mm. From this oil octadionol can be isolated. Its formation takes probably place according to the following formula:

crn co on Octadionol is a limpid thick oil boiling at from 14;2143 C. under a pressure of 22 mm. It is soluble in water, alcohol and ether.

The same product results by boiling methylene acetone (1 part) with water (10 parts).

We claim 1. The herein described octadionols, 0btainable from methylene ketones, which products are limpid oils soluble in water, ether, alcohol and benzene, substantially as described.

2. The herein described dimethyloctadionol, obtainable from methylene-ethylmeset our ha ds in the presence of two subthylketone Which is a limpid colorless oil scnhing wltnesses.

boiling at 148 C. at 18 mm. pressure, soluble GEORG MERLING. [1 5.] in Water, alcohol and ether, its semicarbazone HUGO KOI-ILER. [L. 5.] melting at 209210 C. substantially as de- Witnesses: scribed. WALTER VONNEGUT,

In testimony whereof We have hereunto ALFRED HENKEL.

Copies of this patent may be obtained for five cents each, by addressing the Commissioner of Patents, Washington, I). G. 

